通过钯催化糖基化反应对SL0101及其类似物进行从头不对称合成。
De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation.
作者信息
Shan Mingde, O'Doherty George A
机构信息
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
出版信息
Org Lett. 2006 Oct 26;8(22):5149-52. doi: 10.1021/ol062076r.
Abstract
The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described. [reaction: see text]
摘要
天然存在的山奈酚糖苷SL0101（1a）及其类似物1b - e及其对映体已通过7 - 10步实现了对映选择性合成。这些路线依赖于非对映选择性钯催化的糖基化、酮还原和二羟基化反应来引入鼠李糖立体化学。这些山奈酚糖苷糖部分的不对称性源自酰基呋喃的诺伊里还原反应。还描述了在碱性条件下乙酰基从轴向（C - 2）位置向赤道位置（C - 3）的转移。[反应：见原文]
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